We ALL remember that very first moment when we knew...
When did we begin? How did that happen? What did it feel like? How did you cope?
Was it nylons, heels, a skirt, a bikini, panties, bra…? So many questions and so many of us have similar genesis stories around our crossdressing.
When Did You Start?
At what age did you begin to crossdress?
No Data Found
No big surprises here, most of us seem to have known from a very early age that we had this feminine side to us, or it was awakened as we became sexual in our teens.
But GO GURL, for the late bloomers!
Childhood Experiences and Curiosity: For many, the journey into crossdressing began in childhood or early adolescence. A blend of curiosity and fascination often sparked these early experiments. For instance, one individual recalls, “I started at top end of primary school but because I was caught by my parents and older siblings, I was severely punished,” highlighting a blend of early interest and the challenges faced.
Oh how I recall these long dreams of being a girl while lying in bed. Jennyx
Family Influence and Early Opportunities: Family members often inadvertently provided the first opportunities for these individuals to crossdress. Whether it was through playing dress-up with cousins – “My girl cousins stayed over for a weekend… They dressed me up in their dresses and petticoats, I was so happy” – or through access to clothing, family played a significant role in many crossdressers’ early experiences.
Sadly my mum handled it very poorly when she found out. Jennyx
Self-Discovery and Gender Identity: Some individuals recognized a deeper connection with crossdressing related to their gender identity. As one person put it, “As before is was a feeling that I was born in the wrong body from a young edge.” This suggests a profound sense of self-awareness and the role of crossdressing in their personal journey of gender exploration.
The confusion was what I found hardest. I loved being a boy. I also loved being a girl. Jennyx
Sexual Awakening and Exploration: For others, crossdressing was intertwined with their sexual exploration. Discovering the thrill and excitement associated with wearing certain types of clothing was a common theme. “It started in my early 20s… I got such a thrill out of it. I had to have more!” This highlights the sensual aspect of crossdressing for many.
My first orgasm when dressed litteraly broke my world. I chase that dragon every day. Jennyx
Finding Comfort and Joy in Feminine Attire: Many crossdressers expressed a deep sense of comfort, joy, and rightness in wearing women’s clothing. The sensory experience of different fabrics was often mentioned, as in “I discovered lace and satin felt amazing on my body and made me feel special.”
With the right girl, I love to dress and relax and just watch TV. Though the arousal is often too much to bear. Jennyx
Influence of Media and External Stimuli: Media, such as magazines and online content, also played a role in igniting interest in crossdressing. For example, “When I found my Dad’s Bette Page pin-up porn I knew I wanted to dress and look like her,” shows how external images and representations can influence personal desires and actions.
For me it was the Littlewoods catalogue lingerie section. OMFG! Jennyx
Privacy and Secrecy in Exploration: Many started their journey in private, often due to societal pressures or fear of judgment. The act of secretly trying on clothes was a common theme, as one shares, “I would also sneak into female friends rooms and sometimes take their intimates.”
My journey was also secret, until it was discovered. And then all hell broke loose. Jennyx
Empowerment and Embracing Identity: Ultimately, many crossdressers found empowerment and a sense of true identity through their experiences. Embracing this aspect of themselves led to feelings of fulfillment and happiness, as captured in the sentiment, “I knew then I was a crossdresser and I had a sisterhood I belonged to.”
I am super comfortable as a girl. Or man. I wish everyone was as comfortable with me being a girl as I am, and it remains one of the great unspoken barriers for many of us. Jennyx
Comments left by the gurls...
“I would lie in bed and dream of a fairy godmother who would make me into a pretty girl and everyone would accept me as one then. I would then live my life as a promiscuous lesbian”
“I started at top end of primary school but because I was caught by my parents and older siblings, I was severely punished”
“I was caught stealing my aunts undies …and then she made me dress up for her.. and I am a sissy since then”
“Found that my brother had borrowed a leotard for a scout show. Was curious what would it feel like to wear, so when everyone was out I put it on. It was magical”
“As before is was a feeling that I was born in the wrong body from a young edge.”
“It started in my early 20s. I had chanced to get my hands on a couple of pairs of a particular young lady’s panties and just had to try them on. I got such a thrill out of it. I had to have more!”
“When I was very young, probably 5 or 6, I became attracted to girls clothes…especially when girls would wear pretty dresses for Easter, family events, etc. My interest expanded to everything about dressing as a girl…hair, makeup, underwear, dresses/skirts, shoes, and lacy anklets. I wanted to dress like that.”
“In a school play I had to wear tights and thought they felt really good. Then I snooped around in my mom’s drawer and tried on her bras at a later date. I would also sneak into female friends rooms and sometimes take their intimates”
“I discovered lace and satin felt amazing on my body and made me feel special.”
“It started with trying on pantyhose”
“As a teenager I had thoughts that I should have been a woman but just shoved them aside. But those feelings came back a few years ago and decided to embrace them. Best decision I made.”
“I’m the last of three girls and always played dress up with them. I only wanted to wear a silk pink dress. When my eldest two sisters were two old to play, my closest in age sister would dress me in her ballet costumes and teach me her performances. I was always jealous that she got to do dance and wear such pretty things.”
“I didn’t know about gender back then but I knew I liked the feel of female clothes and designs. It started with some simple white socks but grew into underwear and skirts. Now I prefer to wear knickers all the time and dress fully whenever I can. I love a fancy dress party now!”
“Saw my mother’s bikini and tried it on quite liked it and from there my journey started”
“Funny story actually, my girlfriend and I had gotten tipsy on Halloween and she asked if she could dress me up and do my makeup. I agreed on a lark and we both found it incredibly fun. Ever since then we’ve both been very into it”
“A girlfriend moved out and left garbage bags of women’s clothes, including lingerie. I was very excited by this and tried them on, and even would get dressed up and fuck myself with a dildo. I don’t remember crossdressing earlier, but obviously the spark was there for this event to ignite it.”
“I was shocked when I tried on mom’s pantyhose as to how different and amazing they felt. Everything after that was the same: shocked and amazed. Over 40 years later I still love it like the first day”
“The initial attractions led to my curiosity and finally tried my sister’s clothes out. After which I started to like the feel and comfort of dresses and skirts. And I still crossdress in private.”
“I liked a few particular items from my mom in the beginning. And I was thrilled by a pair of knee high high heeled boots that she had. That was the beginning of my fetish for knee high and especially thigh high boots.”
“First memory was stealing & wearing my sister’s life sized doll’s ruffled panties & top”
“When I found my Dad’s Bette Page pin-up porn I knew I wanted to dress and look like her.”
“Started dressing in my 20’s wearing my wife’s undies.”
“I found I enjoyed the feeling of wearing women’s clothes to be very exciting. I went into my mom ‘s room to try on panty and bra and a pair of clip on earrings”
“I thought i was the only boy in the world who enjoyed wearing girls clothes. I had seen others dress but it was for comedy tv shows. I loved it but was scared to share it with others. I kept it to myself and even got away from it for awhile. One day o saw in a porn magazine a man wearing hose and was like omg that is me. I slowly got back into it and then started deep diving through the internet finding i wasnt alone but onr of many. I knew then i was a crossdresser and i had a sisterhood i belonged to.”
“My girl cousins stayed over for a weekend and we were playing a game. They dressed me up in their dresses and petticoats, I was so happy.”
“I was watching other crossdressers and sissies online and fell down the rabbit hole.”
“I all ways notice that female underwear and clothes were pretty and in some cases so comfortable,”
“When I was about 6 I wanted to wear my cousins pretty Easter dresses. Today they would be called sissy dresses. I still want one.”
“I found a pair of my mom’s pantyhose and decided to try it on. I guess you can say I was hooked from there as I loved the feel of them and how they made my legs look. From there it was stealing my sister’s older bras and dresses that she never worn anymore and it blossomed from there.”
“I think the adrenaline created by dressing and going out is exhilarating. The fear of what could happen. I had a two drinks and people watched. When a guy came up and told me I didn’t pass, but he would still get with me. I told him I was waiting on my girlfriend, finished my drink and left.”
“I had my first bisexual experience at 15 (mutual oral with a friend) and since then have looked for opposite of vanilla with my sexual experiences – crossdressing is ‘it’ for me.”
“I remember a feeling pre-teen of wanting to be a girl, then as a teen I tried on panties for the first time. It wasn’t until my 20’s that I started to buy my own clothes and now I’m addicted to it.”
“My older sister and her friends all looked so pretty in their school uniforms. I would wear her tights and skirt and pretend I was a girl whenever I got chance. I wished so badly I could be a schoolgirl”
“I started about fourteen here and there. I started buying more clothes as I moved out. Mostly stockings and panties. I meet my first Dom at a Fredricks of Hollywood I shopped at. She was kind when I shopped and helpful with sizes with out snickering at me. Eventually she slipped me her number and note that we should talk outside the store. This led to me dressing for her and her husband for a few years eventually as a live in maid/sub to both.”
“I first started experimenting when I was a teenager and found that I loved the feeling and material of some of my mother ‘s lingerie. I slowly started crossdressing and trying on her makeup whenever I got the chance when I was home alone. I found that I really enjoyed it and felt sexy and feminine. Unfortunately I stopped when I moved out in my early to mid twenties because I lost access to women ‘s clothing and such. It wasn ‘t until recently that I started to rediscover my love for it after getting out of a toxic relationship and my ex left quite a few of her clothes and lingerie behind. I started trying them on again and realized how much I missed crossdressing and it ‘s been almost a year since I have been doing it seriously, fully shaving my face and body, wearing makeup, women ‘s jewelry and accessories and presenting myself as a woman on the weekends and whenever I have a day off.”
“First intro was seeing a porn magazine with shemales, but also I loved looking at classic sexy lingerie in catalogs, so I put both together and had my first attempts”
“I was 6 when I first started. Summer camp had a trunk of clothes for us kids to play dress up. I thought the gowns were MUCH more fun than the suits! From there, it was sneaking into my mom’s and my sister’s clothes. When I had broken up with a girlfriend, I decided it was finally time to go full out with dressing and haven’t looked back since.”
“I always adored womens glamour underwear, but never encountered a woman who was keen to dress up in it, so I started wondering why and what it would feel like”
“I did it to help another man get his first same sex experience. I didn’t realize how much I would enjoy it though. So much that I have offered myself up to several different business men. I love being a woman!”
“Home alone dressing in Mother and Sisters clothes.”
“When we finished my room in the basement i was close to the laundry room and had more privacy so i would take my sisters clothes from the laundry and wear it. eventually i got comfortable enough wearing it that i would wear it for my stroke buds who i eventually became their suck friend.”
“It started with panties, of course. I had gotten my hands on a pair of a certain young lady’s panties, and was gripped by a sudden urge to put them on. I loved the way the fabric felt on my penis. It kind of blossomed from there.”
“An older neighbor boy dressed me in his sisters clothes multiple times when I was in second grade”
“I saw my sister’s frilly nighty and panties and had to put them on and found it a huge sexual turn on. I was about 12.”
“I did try a little crossdressing in my preteens while confused about puberty but then stopped until my mid 50s when my wife stopped being interested in sex. I think maybe.it is a bit of frustration that she no longer wears sexy clothes herself but I still find them exciting.”
“I had wondered what it would feel like for months. Then I played sick one Sunday and waited for my family to go to church. Then I ran down to Mom’ s closet and the fun began.”
“Sister dressed me in sexy lingerie and she could see how excited I was when I slipped into lacy panties, that it became a regular occurrence.”
“I was confused but excited by wearing underwear and a ponytail wig of my sisters. In my teens I went a bit further but only went more at university and beyond”
“I was 6 and loved watching my mom get herself together in the morning. Bra panties garter hose slip heels dress or skirt and blouse i wanted that and have every day since then I dream of the day I will start hormones and transition full time as a woman”
“I bought some lingerie for a girlfriend and she wouldn ‘t wear it so I did. I then knew I could buy more because at the store I would pretend I was buying it for a girlfriend. Then I bought a pair of black four inch heels and wore them home, it felt so good.”
“I was alone at my relatives home and then I found some girly clothes of my size and I tried them and fall in love with girly clothes and girly things”
“My mother clothes is where I started”
“Being young, remember trying on my mothers tights many times, moved onto underwear and heels.”
“It wasn’t until my Wife began picking out women’s clothes for me to wear as part of making me submissive in our FLR. I love Her reactions and have learned to love dressing this way for her. Currently She dresses me this way every day and makes me wear them under my work clothes. She even makes me wear women’s clothes to driver Her around town on Her errands. Her pleasure is a huge turn on for me and She’s turned this into something very erotic for me now because it’s connected to Her pleasure, not mine.”
“As a child, I’ve seen lots of movies, cartoons, where the character dressed up as a woman, or even turned into a woman. It seemed fun, so when I had alone time at home, I tried on a couple of my mums clothes, lingerie, and liked it. Ever since then, I was a crossdresser.”
“Had a mistress . She got me started”
“Out of curiosity was in vegas had been communicating with a lady that did mtf makeovers , was losing to much gambling so called her went for a makeover got hooked , could not believe my eyes when she finally let me look in mirror”
“It made me realize how cute and sexy they made me feel and also made me kinda wish I was born a girl so I could wear them and look cute all the time”
“I’ve always had clothing based fetishes… was just 1 step further to dress in them myself”
“Found my sister’s clothes in the dryer one day while I was home alone and tried on a cute orange satin thong, red stockings and a black skirt. I liked it so much I took the panties and wore them under my boy clothes for the rest of the day, sometimes even in public or at school.”
“The sensual and erotic feeling of trying on and wearing panties, and then a satin and lace cami, I was hooked!”
“The first time I saw a Bra, in our complex shared laundry room I stole it as I had an urge to put it on”
“I suppose best described as a compulsion I also felt a lot of guilt for what I did and to some extent now continue to do so. During my 20s whilst dating I would buy lingerie then clear it out and expected the desire to crossdress to go away once married. Of course, it didn ‘t!”
“I was mostly curious what it would feel like to wear pantyhose and a women’s thong and I’m still experimenting, though I do find wearing heels to be fun!”
“It just seemed the right thing for me”
“I didn ‘t know what to think I only knew that it felt right for me.”
In the next post...
We will dig into how often we release our true selves, how often do we dress up and WHY do we do it?
Explore The Whole Survey...
Nearly 200 crossdressers took my survey over the last week, sharing who they are, sometimes their wildest fantasies, even their most outrageous stories. And there was frustration and sadness in some answers too. All of these emotions I relate to. The survey is still open here and data does update with the dynamic charts here. Thank you, you gorgeous gurls!
When did we begin? How did that happen? What did it feel like? How did you cope? So many questions and so many of us have similar genesis stories around our crossdressing.
So gurls, how often do we indulge in our inner femme and get dressed in panties, bra, heels, stockings and a cute dress? The wardrobe awaits, let’s open up and explore what we find!
What is it about our gurl clothes that seduces us so deliriously? What does it feel so, right, good, sexy, relaxing and wonderful?
That’s right, to have a peek inside your wardrobe. Is it hidden or on display? How extensive is it and does your partner know about your femme side? And if so, how do they feel about it?
Who do we like to get it on with, while in our feminine energy…. Let’s get into the sticky details. What our past, present and future lovers look like. Always while in heels of course. Can I also just state now how much I have adored this whole prcess? Connecting with so many wonderful gurlies and hearing your deepest and darkest secrets. It’s been my honour.
So what does fire you up the most? I asked. You shared….To get us in the mood, I asked about threesomes first, but this final section is simply the cherry on top of the whole survey. We also shared about porn and what we watch. What fantasies fill our panties the most? Buckle up, it will be wild!
First of all, thank you to every brave gurl who chose to share her deepest secrets, desires and even pain with us all. You are AMAZING! And a little bit sexy too.Second, I am no maths whiz or expert analysis, so much of my thoughts here are what struck me most, rather than perhaps statistically significant. And of course I would love your thoughts too.